Ethyl 2-chloropropionate → Ethyl 2-(3-fluoro-4-nitrophenyl)propanoate

HRID 238921

反応式

HRID 238921 の反応式
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH2:17]([O:19][C:20](=[O:24])[CH:21](Cl)[CH3:22])[CH3:18]>CN(C=O)C>[F:7][C:8]1[CH:13]=[C:12]([CH:21]([CH3:22])[C:20]([O:19][CH2:17][CH3:18])=[O:24])[CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

参加物

5

反応物 3

HCID 10807Ethyl 2-chloropropionateHCID 738951-Fluoro-2-nitrobenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 12879863Ethyl 2-(3-fluoro-4-nitrophenyl)propanoate収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of potassium t-butoxide (20 mmol) in DMF (20 mL) was added a mixture of 2-fluoro-nitrobenzene (10 mmol) and ethyl-2-chloropropionate (10 mmol) at 0° C. dropwise. After being stirred for 10 min at 0° C., the mixture was quenched by 1 N HCl solution, diluted with water and extracted with diethyl ether several times. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:10) as eluant to afford ethyl 2-(3-fluoro-4-nitrophenyl)propionate (1-1, SU-654).

後処理

  1. customthe mixture was quenched by 1 N HCl solution
  2. additiondiluted with water
  3. extractionextracted with diethyl ether several times
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-0fbf866d9f15456097d65ecc3742a89a
出典データセット
uspto-grants-2014_02
特許番号
US08642657B2

関連ノート

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